Crime Doesn't Pay?
by TheBoredBoot
Summary: Who would've guessed he survived being eaten. Roman Torchwick now free from his services to Cinder was looking for the quiet life now, ironic that he of course ran once again into the girl that caused him so much trouble. That beautiful and adorably innocent girl. Looks like its time for one last score, the target her heart. Who said that crime doesn't pay? Rated M for reasons


**Crime Doesn't Pay?**

A one-shot by TheBoredBoot

AN: To those reading this please know that this is just purely on a whim and suggestion, while Rosewick is a guilty pleasure of mine sadly there's not much I can really do for it. This is just a bit of fun for me so I hope you all enjoy. RWBY and it's characters are owned by RoosterTeeth.

This takes place right after the events of Vol. 3 with a twist.

In the burning wreckage of a crashed Atlas airship the corpse of a recently killed Griffon twitched, movement of something struggling to escape.

"God damn this stupid beast!"

Struggling with the last bit of flesh keeping him trapped inside the now dead Grimm Roman Torchwick, using a small pocket knife cut through the last seam of muscles on the Griffons throat. After one last thrust the skin parted and he burst out of the creature gasping, the first breath of fresh air filling his lungs smelling like heaven as he shakily stood, glaring down at beast that had swallowed him whole before examining himself.

"Oh how disgusting, now I'm going to have to get a whole new outfit and burn this one, you dirty creature." Kicking the corpse as it began to give off that ghastly black smoke, signaling it was going to dissolving away. Shooting it one last glare Roman took a few steps back and looked around the area a second before realizing where he was.

From where he stood he could see the ruins of Beacon Academy and the CCT, smoke still rising from where the fighting had started fires all over the area, giving the ruined city an ominous aura as the darkening sky opened up and the rain fell. Judging from the area he could only guess that the airship they had stolen went off course and crashed along the edge of the residential district. The sight of all the destruction and devastation from the attack oddly enough saddened him, his thoughts going back to first starting this job.

" _It started off a simple job yet here we are now, partly responsible for the destruction of a whole Kingdom."_ Roman sat down and sighed looking up into the sky, the shattered moon and the stars shining the only light besides the smoldering fires that still burned much like his mood. Thinking back on it all his thoughts drifted to the night it all started, the night that foolish girl had gotten in his way. Shaking his head Roman ignored the memory, the only desire he had now was to find the final dead-drop, pick up his money, and go on with his life. Getting back to his feet he gave another sigh and cracked a grim smile. _"Oh well after all it was only a job, nothing personal Red…"_

 **Two months later**

Far away from where he had had his brush with death, Roman torchwick sat in his now favorite restaurant enjoying a drink. During the couple months since the fall of Beacon he had spent his time collecting his money, setting up a new identity, and finally finding a place to lay low. His ears still peeled for any news of the White Fang or Cinder's faction meant at first he was rarely relaxed, but now after a couple months he figured that his old boss thought he was dead something that he was extremely grateful for now, his thoughts now on the dark haired woman who once ordered him around.

"Cinder was quite the looker don't get me wrong, but I guess I have a taste for much more innocent morsels," He said under his breath, taking another gulp of his drink enjoying the feel of the alcohol, but at the mention of innocence brought her image to mind. The dark hair, her silver eyes, that look of genuine innocence. Roman sighed and shook his head again, turning to look out the window and he suddenly spat out his drink in shock.

"Oh you've got too be kidding me…"

Just outside walking along the side of the building he spotted the unmistakable red hood of the girl who had caused him so much trouble, actually now that he thought about it she was the reason he had gotten eaten too.

Getting up and turning so he wasn't facing the window Roman grabbed his drink and swiftly moved to one of the corner tables, the shock at running into her again made his heart pound for some reason. Taking another deep breath he looked across the way to a decorative mirror on the wall, he could see that even without his hat he looked relatively the same, a little more rugged due to the 5 o'clock shadow on his face and his much darker unkempt hair he figured he was still recognizable, in his newly cleaned and tailored white suit, complete with black pants and matching shoes.

As if on cue the door opened and from the corner of his eye Roman saw that it was her who had entered the restaurant, making her way to where the receptionist was.

"Why hello miss what can I do for you today?" The man working the podium said politely bowing his head in greeting.

"Oh hello," Ruby said nervously returning his greeting before looking around again. "I was told by one of the locals that this was a good spot to grab a bite to eat, I was also going to ask if there was a restroom I could use as well?"

"First door on your left," the man said gesturing to the hallway behind him. "And when you are finished you can take a seat anywhere you want."

"Thanks," Ruby chirped dashing off to the restroom unaware of her former adversary watching her.

" _I should probably sneak out now while I have the chance,"_ he thought to himself still watching the hallway she went, but still not getting up to leave. After several minutes of just sipping his drink Roman couldn't help but think again. _"Why am I not leaving? I couldn't be hoping she'll see me, could I?"_ Hearing the sound of her footsteps returning he resisted the urge to turn and look, stead he just listened to their conversation occasionally sipping his drink.

"Please pick a seat miss and I'll get you a menu," the man said following Ruby as she walked towards the center of the dining area.

"Ok, and thank you again." Ruby said giving the man a friendly smile walking to the table by the window. Taking her seat she couldn't help but notice how empty the place was, beside an elderly couple and one or two more customers the place was empty forcing Ruby to ask. "I'm sorry, I don't mean to be rude but is this place always empty?"

The man gave Ruby a sad smile and shook his head. "Actually most folk have gone and left town, the fear of more Grimm and White Fang attacks drove them off. Truth be told, the last few months beside you and your group of friends we've only had one person stay in town longer than a week, it's that gentleman over there." The man said pointing over to where Roman was sitting.

" _Fuck!"_

Turning his head and locking his green eyes with the young huntresses silver ones, trying to play it cool Roman chuckled. "Haha what were the odds we'd run into each other again, huh Red?"

Barely a second passed before there was a loud crash and the table Ruby was seated at was knocked over, drawing Crescent Rose her eyes widened in disbelief at the sight of Roman who calmly took another swig of his drink flashing her a half smile.

"Oh cmon now Red, did you really think I'd go down that easy?" Going to take another swig from his drink he stopped realizing that it was empty, sighing he motioned to the waiter for another before turning his gaze back to Ruby. Seeing how she wasn't putting away her weapon he sighed and held his hands up in mock surrender. "Look Red I'm unarmed and I'm sorry, so you can put that oversized garden tool now away and have a seat," gesturing to the seat across from him.

Ruby didn't move, her eyes still wide in disbelief, the last memory she had of him was the Griffon swallowing him whole, seeing him alive and well again brought forth a strange feeling in her chest that she didn't understand. _"This is impossible, I saw that Grimm eat him."_

Roman could see that she was having a hard time coming to terms with seeing him again and broke eye contact with her, his voice taking on a strange tone as he muttered, "well anyway it's oddly nice to see you again Ruby. I don't know why but it is."

Hearing Roman's strange tone Ruby stopped glaring at him and sighed, switching the scythe back to compact mode she then turned to the waiter and apologized before helping him right the table. Hesitating for a second more she then sat across from Roman and fell silent, her eyes not leaving his face and even though he couldn't meet her eyes again she could feel he was still looking at her. Ruby's heart beat a little faster knowing this and she had no idea why, _"I mean he is pretty handsome."_ she thought out of nowhere surprising herself.

After a moment of awkward silence between the two the waiter returned and took their orders, Ruby unsure of what to get and limited on lien begrudgingly accepted Roman's offer to pay for dinner. "It's my way of saying I'm sorry and that there's no hurt feelings Red," Roman reasoned taking another swig of his drink. "I have no personal grudge against you or your friends, everything that has transpired in the past has purely been because of a job, and as distasteful of a job it was I was required to follow through with it."

"But why take a job like that?" Ruby asked in a confused voice. Seeing this side of Roman she honesty didn't know what to make of what she's was feeling, brushing her hair back she then asked quietly. "What happened that made you end up like this Roman?"

"Ha I'll tell you what Red." Roman chuckled. his laugh obviously hiding his emotions as he took another swig calling for the bottle. "You help me finish this wine and have a meal with me and I'll tell you everything you want to know, it'll be my treat. Sound like a deal?

Hesitating a sec longer Ruby thought about it and then shook that last hint of uneasiness away, giving him an honest smile she nodded.

"Alright you have a deal."

 **Two hours and three bottles later**

After their meal, while she and Roman had sat talking and drinking the night away her scroll had gone off multiple times. When Ruby had finally decided to answer is she made sure to put her worrying friends at ease letting them know that she was ok, her meal was going on a little longer then she had planned so she told them not to wait up. Now no longer sitting across from Roman she had no idea when she had joined him in the booth seat but now found herself leaning against him, his arm gently around her shoulder holding her close.

This was the first time she had ever drank before and,the alcohol made her feel all wonderful and bubbly, the worries and sorrows she had been holding inside melting away as she leaned against him Roman. The longer she stayed there the more she noticed an odd sort of warmth in her chest that she couldn't understand.

Laughing a little longer Roman pulled out his pocket watch to check the time and gave a sad sort of frown. "Well it's gettin late Red, I'm going to head over to my hotel room and call it a night." Standing up and pulling away away he gave her a little smile. "This was nice Ruby I really enjoyed seeing…"

Roman stopped mid-sentence feeling Ruby grab his hand stopping him, the blush oh her face either from the alcohol or something else causing him to gulp. _"Damn she's cute."_

"You… you called me by my name again," Ruby said blushing an even deeper red. Letting go of his hand she began toying with the hem of her skirt, looking away from him for a moment before she asked in a low voice, "hey Roman. Would it be ok if I came with you? You know so we could talk more."

Hesitating slightly Roman then nodded slowly, his green eyes meeting her silver ones as a surprised desire rose up in him. "Yeah sure," he coughed nervously leaving his money on the table before Ruby linked arms with him. The two of them smiling then left and made their way out of the restaurant heading towards the the slightly shady looking hotel that Roman was staying in, both nervous yet excited for whatever was going to happen next.

 **Ten minutes later**

Roman's hands shook slightly as he unlocked his door, completely aware of how close the young huntress was behind him he couldn't help but be slightly nervous as he thought, _"great I didn't expect to run into her again, let alone have her come back to my room. Looks like little Red is just full of surprises."_

Following Roman inside Ruby couldn't help but feel the shiver of a thrilling sense fear, they had been enemies at one point but after their meal and drinks she know that for him it was much more complicated, her expression turning sad as she recalled his story leading to a life of crime, then back to what he had said to her on the top of the airship during their last fight.

" _I can see why he has such a hard time seeing the good in the world now, after being beaten down by it so many times it only makes sense to want to give up and hide from world."_

"Well I actually have some more wine here if you'd care for another glass," Roman said interrupting his guests train of thought as he roamed his eyes over her again admiring how how she had matured over the time since they had last met. Meeting her eyes again and catching sight of her face turning red he then realized that she had caught him staring at her body, quickly breaking eye contact Roman began fumbling with his words trying to use the excuse that he noticing her change in wardrobe and how it made her appear older.

Ruby laughed quietly at this and without even thinking took a couple steps forward coming right up against him, getting on her tippy toes she stretched up pursing her lips and waited, her body pressed lightly against Roman who had froze at her touch.

Looking down at her trying to understand why he blinked once and then pushed the thoughts and reasoning away. With his heart pounding in his chest and his hands shaking worse than before Roman gently reached one hand around placed it in the small of her back leaning in, wetting his lips once before meeting hers for the first time.

" _Her lips taste like roses and strawberries, well that and the wine,"_ Roman thought closing his eyes deepening the kiss, his other hand nervously moving to the back of her neck.

Maybe a minute passed. Maybe an eternity before they broke their kiss and all Ruby knew was that she was taking a risk with him, and she didn't give a damn.

Opening her eyes she found his green ones staring back at her, the two of them slightly out of breath and red in the face looked at each other nervously, for Ruby there was a new feeling in her heart while for Roman, rekindled in him was a feeling he hadn't been able to feel in years.

"Ruby… I'm sorry I," Roman muttered starting to pull away slightly only to have Ruby's lips collide with his again. Stumbling backwards in surprise he tripped and fell back onto the floor, the young huntress following him knocking the wind out of his chest from landing on him.

"Roman! I'm so sorry. I meant we just kissed, I was confused so I went to kiss you again. Now you fell and I landed on you." Ruby cried covering her face in embarrassment while Roman struggled to catch his breath, half wheezing, half laughing at how cute and innocent Ruby was.

"It's ok Ruby," Roman reassured after catching breath again, looking up at her smiling bashfully their faces once again inches away from each other. Having Ruby straddling him still Roman but his tongue struggling to control himself, her innocence just driving him crazy. Deciding to take a risk he said a careful tone, "why don't we try this again Red." His hand reaching up and caressing Ruby's cheek as he leaned up initiating the kiss this time, the disbelief that this was happening overridden by the shock or Ruby reciprocating the kiss, her hands going to either side of his face holding him in place.

After a moment the two of them broke apart again, a thin strand of drool connecting them as they panted heavily staring at each other, this forbidden passion the two of them felt urging them further.

"Roman…"

"Yes Red…"

"I'm scared, I mean I've never…" Ruby's voice faltered as her face turned the shade of her hood, her hands going to cover her face were stopped by Roman who held her gently, his eyes not leaving her face.

"Only if that's what you want Red, I promise I'll be gentle as possible but I can't say it won't hurt." Roman whispered pushing himself up so he was sitting Ruby in his lap facing him, his heart racing as he studied her face looking for what she truly wanted.

Biting her lip and still blushing Ruby nodded nervously and climbed off Roman before smoothing out her skirt, hands noticeably shaking as she tried to get her nerves under control mentally preparing herself. Looking past Roman towards the bedroom Ruby couldn't help but feel her heart skip a beat and wanting to prove her resolve to him reached up and unclipped her her hood and cape letting it fall to the ground behind her.

Without another word Roman gently picked her up princess style and carried her towards to the bedroom, the door closing silently behind them as Ruby's scroll began vibrating in the pile, the contact Yang Xiao-Long flashing across the screen.

After blushing and looking away while Roman took off his shirt and pants, Ruby gasped slightly when he came up behind her, his hands gently resting on her hips as his lips found her neck gently teasing the flawless pale skin.

"Are you still scared?"

Steeling herself, Ruby nodded and slowly turned around, to her virgin relief Roman was at least still wearing a pair of red and white striped boxers. Laughing quietly to herself in relief looked up into Roman's face, he had a calming and reassuring smile on his face, but Ruby could see in his eyes that behind his calm demeanor was a hunger that both scared her slightly and awoke a hunger of her own inside her.

Leaning in Roman gently kissed her again while his hands went to the front of her top undoing the corset like bindings and buttons, the kiss seemed to calm Ruby as she was fidgeting less during this, her lips eagerly meeting his own as she wiggled her shoulders and moved her arms allowing Roman slide her top off.

When her top hit the floor Roman pulled away from the kiss slightly, unable to help himself from admiring body as Ruby blushed again partially covering herself, embarrassed and self conscious of her figure she whined in a low voice. "Roman, please don't stare. It's embarrassing."

Roman chuckled and gently reached cupping one of her breasts drawing a quiet moan from her while his lips moved to her ear, the softness of her skin combined with the smooth fabric of her bra sent another wave of arousal through him. "No need to be embarrassed Red, trust me when I say you're beautiful." He whispered before kissing her neck again, moving down further to her collarbone as another moan escaped her lips.

Internally Ruby screamed from embarrassment, the feeling of Roman's hands and lips against her skin causing her to moan again her hands clapping across her mouth to hide how flustered she was with his lips trailed further down to her belly. With her legs shaking and about to give out from nervousness Ruby panted and in a hoarse voice moaned, "Roman. Please I need to sit down for a sec."

"Of course Red," Roman said softly a faint hungry growl in his voice as he laid her back onto his bed leaning over her. Looking down at Ruby he gave her a questioning look to which she nodded and raised her legs up blushing even harder as he lightly trailed his hands down her sides, reaching to her hips, carefully watching and gauging her response to his every touch.

Hitching his breath Roman gave a small gulp as his hands finally made it to Ruby's belt, her innocent silver eyes looking up at him as he slowly undid the belt before sliding the skirt off her. The bullets on the belt jingling slightly as he dropped it down onto the floor. Lying there before him wearing only a matching set of crimson bra and panties, a darker pair of rose print stockings and a blush on her face, Ruby reached her arms up and wrapped them around Roman's shoulders bringing him down to her.

At this point Ruby was squirming at every touch and movement Roman made, the burning heat inside her driving her crazy causing her to unconsciously rubbed her thighs together in anticipation as her mind began to go blank, a feeling of dampness becoming noticeable between her her legs as the purely instinctual and primal desires of one in the state of arousal slowly started to take hold of her. Kissing him again, the courage from the wine and knowledge that she couldn't back away from this now pushing her further then she had ever gone.

His hands tracing the subtle curves of her body Roman watched her, Ruby's eyes were closed as she writhed beneath his gentle touch, the moans of her pleasure though quiet as they were rung in his ears as he caressed her.

"R-R-Roman," she moaned one last time opening her eyes. Tears of ecstasy shining as she drooled slightly.

That was the last straw for Roman. Clenching his jaw he placed two fingers over Ruby's lips quieting her down, then slowly traced them down brushing past her breasts and flat stomach before tenderly passing over her moistening panties pulling them slightly to the side.

The young huntresses breaths continuing to get heavier until they stopped in surprise, the feeling of his one of his fingers gently massaging her now dripping womanhood sending a shiver of pleasure through her body, his fingers deliberately teasing her lips but going no further than that. Ruby feeling like she was on the edge reached up and began massaging her breast, on instinct trying to give herself the final push and succumb to her pleasure.

" _Wow she's really getting into this,"_ Roman thought mentally licking his lips looking down at her. _"Maybe little Red could use some help."_ Using his other hand he pulled Ruby's bra down and and placed his lips over one of her breasts eliciting a squeal of surprise from the girl, but Ruby didn't resist in fact she pressed his face harder against her chest moaning Roman's name until she cried out suddenly spasming against the hand now deep between her legs.

After a moment of nothing but the two of them breathing heavily Roman gently moved above her and stared into her eyes, the two of them reveling in the ecstasy of each other's touch. Pulling his hand from between her legs Roman looked down at at Ruby with hunger in his eyes, placing the two fingers that seconds earlier were inside of her into his mouth savoring her taste, a low chuckle escaping him as she gasped at his action.

"I think you're ready now Red," he said is a husky under tone, his own arousal causing him to be bursting at the seams of his boxers which she finally noticed and blushed at. Her hands covering her eyes for a moment before she nodded in agreement removing them and looking up at him.

Gulping once as Roman freed his erection and pressed it against her entrance Ruby whispered, "I'm ready Roman. Just please… Please be gentle." A hint of so many varying emotions in her voice, ranging from fear and apprehension, to hunger and arousal.

Nodding Roman began pressing against her, his hardened member slowly spreading her open until she whimpered once, nails digging into his shoulder as she gritted her teeth. The sharp pain of her hymen being torn dulling quickly due to her aura. He was inside her, they were one in every sense of the word.

" _She's even better then I could've ever dreamed."_ Roman thought struggling to control himself, the feeling of Ruby wrapped tightly around his cock just feeding into his desire for the girl, but then her words echoed in his mind calming him.

" _Please be gentle Roman."_

" _Alright then Red,"_ he thought smiling again. _"I'll be gentle on you just this once, you are after all allowing me the honor of being your first something that I doubt either you or I will ever forget."_ Still thinking Roman was jolted back into reality when Ruby gently reached up and touched his face.

Looking up at him with tears in the corner of her eyes Ruby whispered. "It doesn't hurt as much now Roman, it's actually is starting to feel good, please don't stop."

"Oh don't you worry my little Rose," Roman whispered back giving her another kiss. "This isn't going end, we've only just begun." Starting very slowly at first he began to thrust inside Ruby, the young girl naturally beginning to shift against him in sync with his movements evidence that she was indeed going to be a natural.

Even through the haze of alcohol Ruby knew what was going on, her lustful gaze looking up at the man above her, inside her, together with her. Ruby could only think with great satisfaction, _"looks like I've become Roman's woman now not that I'm gonna complain."_ His movements she noticed becoming faster and more frenzied while she felt a heat building in her womanhood. Without even meaning to there was a flash of rose petals and Ruby found herself atop Roman moaning as her body moved on it's own bouncing so that Roman could penetrate deeper into her.

Disoriented from Ruby's semblance Roman grunted in surprise as the girl bounced upon him, the pleasure obvious from the expression on her face a sight he thought he would only see in his dreams. The feeling of her flesh smacking his, the sound of her moist snatch swallowing him whole, it was heaven on earth. With each bounce against him she felt his cock within her seem to throb more violently, his breathing like hers becoming heavier with each passing second.

As the minutes passed and she continued to bounce upon Roman, that heat that she felt deep within her finally reaching its peak. Crying out sharply as Roman groaned in arousal her body spasmed as lights flashed in her eyes, feeling as if he had gotten even bigger inside her Ruby felt a burning heat shoot within her as she came for the first time. The feeling of Roman's white-hot seed shooting into her sent her body into another convulsion of orgasmic pleasure. Collapsing onto Roman she gasped trying to regain control of her breathing, the once criminal only fairing slightly better than her as he to gasped.

After laying together for several minutes regaining their composure Ruby shifted and propped herself up allowing Roman's semi-erect member to slip out of her, neither of them paying attention to the slight blood of her virginity that leaked out along with his seed. The two of them were more occupied with each other as Ruby moved to lay beside him, her silver eyes clear and focused as she leaned up and kissed him.

"That was amazing Roman, but now…" Ruby fell silent and shifted her gaze away for a second before continuing. "So are you going to leave?"

Roman felt his heart clench, normally he would just say a lie and then disappear the next morning. But now…

Roman sighed and gently stroked the young huntresses cheek. "Don't worry Red, I'm going to stick around for you. I was just a criminal looking for the next big score but you know what I found Ruby? I found my big break, the biggest heist with the greatest payout of all, and that was your heart Ruby." He said turning red staring into her eyes. "If you'll let me, I'd love to steal you away and make you mine."

Hearing his words Ruby blushed as well. Closing her eyes she laid her head against his chest and gave a small laugh. "I'm already yours Roman, I gave myself to you after all but now we have another question to ask."

Raising an eyebrow in question Roman looked at her before his eyes widened in surprise as he felt her hand trail across his torso before gently wrapping around his dick, his gaze turning back to her as she opened her eyes again a look of hunger visible.

"How about you give yourself to me again as payback for all the trouble you caused?"

Grinning Roman licked his lips as she began stroking him him to full hardness again, his desire for her ever growing as he moved above her again. "Alright little Red, we'll keep going but don't expect it to be as gentle this time."

"I was hoping you'd say that," Ruby moaned kissing him again. The two of them spending the rest of the night in the passionate throes of each other's embrace, not knowing or caring what the future held for them. The only thing that mattered was that now they were together. A forbidden love, brought together by their base primal desires.

AN: Thank you everyone for taking the time to read my little one-shot Rosewick story. Honestly it really is a bit of a guilty pleasure and I may have enjoyed writing this a little too much but whatever to each their own. This was actually an idea I was mulling over for a bit and it turned out rather nice. While I am in the middle of a couple projects I've decided that I'm going to start considering requests for other one-shots from you "the readers." So if you have an idea feel free to shoot me a message or leave it in a review and again thank you for your time. As always any reviews and feedback are encouraged and appreciated, so feel free to like and favorite these stories and stay turned for whatever comes next.

Regards,

TheBoredBoot


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